


Beautiful Boy

by frumpkinisfae



Series: CR2 Kinktober 2020 [1]
Category: Critical Role (Web Series)
Genre: Caleb Widogast Deserves Nice Things, Dirty Talk, Dom Essek Thelyss, Kinktober 2020, Light Dom/sub, M/M, Naked Male Clothed Male, POV Essek Thelyss, Praise Kink, Sub Caleb Widogast, T-dick stimulation, Teasing, Trans Caleb Widogast, Trans Essek Thelyss, Vaginal Fingering, not mentioned but he is
Language: English
Status: Completed
Published: 2020-10-08
Updated: 2020-10-08
Packaged: 2021-03-08 03:07:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,899
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26888620
Author URL: https://archiveofourown.org/users/frumpkinisfae/pseuds/frumpkinisfae
Summary: Essek has spent the last few moments leaning into Caleb, reading over his shoulder. He relishes the blush that colors the human’s pale skin. Lightly tracing his fingers through the wisps of ginger hair not caught by his partner’s ponytail, he takes care to gently graze the sensitive blushing neck.If he were a better man, he’d do away with teasing the poor boy. However, Essek finds that some modicum of wickedness often results in pleasure.
Relationships: Essek Thelyss/Caleb Widogast
Series: CR2 Kinktober 2020 [1]
Series URL: https://archiveofourown.org/series/1961788
Comments: 10
Kudos: 95





	Beautiful Boy

**Author's Note:**

> This is entirely porn. Enjoy!
> 
> This is my day one of Kinktober for praise kink! Of course, Caleb has a massive praise kink and Essek loves it.
> 
> I'm a bit behind on Kinktober, but I intend to catch up in the next few days.
> 
> I'm a trans man who loves trans men so honestly, this was so easy to write.
> 
> Please note that there is some AFAB terminology used for Caleb's front hole, specifically "cunt" and a lot of description of it. There is no AFAB terminology used for his T-cock is referred to as a "cock" and "dick". His breasts are also mentioned and described. In my personal interpretation, Caleb has little to no bottom dysphoria and has fluctuating (between low to high) top dysphoria. Dysphoria is not mentioned within this fic, and Caleb is adored not in exception to his transness but including it. If any of that may upset you, please take care of yourself!
> 
> Thank you and enjoy!

Essek has spent the last few moments leaning into Caleb, reading over his shoulder. He relishes the blush that colors the human’s pale skin. Lightly tracing his fingers through the wisps of ginger hair not caught by his partner’s ponytail, he takes care to gently graze the sensitive blushing neck.

Shivering at the touch, Caleb’s eyes dart from the page he was so diligently reading toward Essek. Ever so sensitive, Essek’s boy is. The drow knows that Caleb has difficulty focusing in proximity, especially with such gentle touching. While he may be frustrated at the disturbance, Essek can practically feel the human’s pulse thrumming with excitement.

If he were a better man, he’d do away with teasing the poor boy. However, Essek finds that some modicum of wickedness often results in pleasure.

“Caleb, would you mind letting me know what passage you’re on?” Essek intones, his lips only centimeters from Caleb’s ears. “I find that dissertation fascinating.”

“Er- Tenke’ate posits that the somatic component of, mm- the Resonant Echo spell has similarities more in tune with the Polymorph, hn- spell, which denotes the possibility that the echo is more material than immaterial,” Caleb murmurs, only briefly pausing to let out little breaths as Essek continues to dance his fingers across the human’s ruddy skin.

When Essek senses that Caleb has said all he will, he traces his finger from his jaw slowly to rest under his chin, passing through the soft ginger curls of his beard along the way. Slowly, but with some strength, he tilts Caleb’s head to face his own. Caleb allows without protest, even dipping his head into Essek’s fingers with fluttering lashes.

Holding his face barely an inch from his partner, Essek asks, “And what do you think my dear?”

Already the darling boy is slipping into his submissive headspace, just barely so, but enough that Essek knows that words and movements have already slowed for Caleb.

With a gently stuttering breath, Caleb says, “I-uh, I agree. A resonant echo, while similar to, mh- the Duplicate spell that clerics, eh- possess, it is actually more akin to the Simulacrum spell. Unlike the, ah- Simulacrum spell, the material component is the obsidian and dunamantic footprint of the subject, rather than, mh- any polymorphed item.”

Essek lets a proud smile spread across his face, “My darling boy, you always impress me with how clever you are.”

As expected, Caleb practically melts at the words. First from the pet name, second from the compliment.

So pliant and obedient, Essek adores how easily Caleb falls weak under kind words and loving tone. Having described it before as a feeling akin to drinking a warm beverage mixed with gooseflesh from music, the drow has learned that Caleb feels every word deep in his core.

Essek wouldn’t be surprised if Caleb has already begun to drip.

“Oh, darling, do you like it when I compliment you?” Essek asks as he begins to card his hand through a lock of ginger hair.

Fervently nodding, Caleb’s eyes are already glassy and dilated. Essek’s eyes soften at the sight and he leans in to plant a gentle kiss on the darling boy’s plush lips. As he pulls away, Caleb attempts to follow the drow’s lips, yet he is stopped by a gentle hold on his jaw.

“A bit desperate tonight, hm?” Essek cups both sides of the human’s jaw. “You’re lucky, darling, that you’re so beautiful I could hardly ignore you.”

As Essek leans in for a deeper kiss, he feels the human’s quiet plea of “please” against his lips. 

And of course, it sends Essek into a passion.

Kiss after kiss, the drow explores Caleb’s soft lips and warm mouth, occasionally nipping the human’s lips to chase the desperate little moans he gives. All the while Essek holds the back of his neck and side of his hip to guide the enraptured human to the chaise lounge in the study.

Breaking away from the desperate kissing, Essek gently guides Caleb into lying on the velvet piece of furniture. Entirely clay in his hands, the human lays down easily as long as Essek’s hands never leave his body.

“Such a precious boy,” Essek remarks at the half-lidded man below him. “You never cease to amaze me with what a good boy you are. I need not even use a verbal order for you, since you can’t help wanting to carry out my every wish.”

Caleb practically vibrates with the attention, moving his arms across the chaise lounge to try to get a handhold. He’s such a tactile boy.

“Yes please, Essek,” Caleb moans into the air.

Unlacing his silk belt, Essek opens Caleb’s casual robe revealing the expanse of pale freckled skin. Essek can’t help but halt, feeling gratitude and pride wash over him as he gazes at this man he was lucky to love.

His decolletage is entirely dusted with freckles giving way to more clear porcelain skin on his breasts. The soft full peaks are completely exposed, with his rosy pink nipples pebbled in pleasure. Wisps of hair decorate this whole space and gather more thickly as they reach his stomach. Around his hips, the freckles return slightly in their intensity, and between them, a tantalizing trail of hair beckons Essek to remove Caleb’s underthings.

Wasting no time, Essek hooks his fingers through the waistband of Caleb’s light blue slip, pulling them slowly down the human’s trembling legs.

At the end of the trail, his hair culminates in a thick bush above his lower lips, manicured by Essek in their bathtime liaisons. The lips in question can easily be seen in all their soft beauty, reddened, and plumped by the extra blood flow. He can see the glistening of wetness throughout the whole crease, as Caleb can’t help but leak like a faucet when aroused. His bright red and throbbing cock peeks out from between the upper nexus, reminding Essek of the inner bud of a pink rose. Unlike Essek’s own, Caleb’s lips are plump and are constantly met at the seam, hiding most everything except the most erect presentation of his cock.

Caleb gives a breathy moan at the exposure and rubs his legs together in bashfulness as Essek drinks the sight of him in.

“Gorgeous,” Essek leans over the prostrate man, delighting in the sharp breaths and moans he can eke out from only words and exposure. “Absolutely gorgeous. I could look at you all night. Might tie you up, leave you posed like a handsome statue.”

“If you wish,” Caleb breathes out, eyes barely open. He has entirely sunken into his submission.

Essek lightly chuckles at his darling boy, enjoying how easily blissed-out Caleb is, “Tonight, I don’t believe I will. Since, my darling boy, touch is far better than just sight.”

Caleb nods slowly, but Essek isn’t even sure that he’s understood anything he’s said for the last few seconds, “Darling, may I touch you? Do you want me to pleasure your gorgeous cunt?”

Canting his hips up in excitement, Caleb pleas, “Touch me, Essek. Please touch me.”

With a grin, Essek obliges.

At first, with just a gentle touch, Essek’s long fingers graze across the entirety of Caleb’s plump lower lips, paying no particular attention to any place. He gingerly guides his fingers through the alcove of Caleb’s inner thighs, cupping his whole cunt in his hand. Essek always enjoys the feeling of holding Caleb’s entire manhood in his hand, flush to its entirety, enjoying the warmth and softness of his cunt.

“Ah, mmh! Ah, please,” after a few rounds of this, Caleb begins canting his hips again, impatient, or just desperate for more. 

Essek leans down to Caleb’s face, delighting in the beautiful agony of his expression, “What do you want, darling boy? Do you want me to touch your cock? Or would you like me to play with you cunt?”

Caleb’s hands practically throw themselves into Essek’s robes, gathering tight fists of brocade, “Both! Mmh, either. Please…”

Once again, Essek’s persona softens and he leans down to give his lover a gentle soothing kiss, “Of course, darling. Anything for my handsome boy.”

Breaking the kiss, Essek twists his fingers through the lock of hair that came loose from Caleb’s hairstyle placatingly as he guides his other hand slowly down to the human’s mound.

Standing up to his height once more, Essek brushes his fingers between his partner’s plush lips, gathering up his arousal before circling them around his throbbing cock.

Wetting Caleb’s beautiful little cock to ensure any stimulation is smooth, Essek captures the base between two of his fingers. Caleb immediately bucks into the sensation, releasing a loud hum of pleasure before Essek starts to stroke.

Slowly, up and down, Essek rubs his lover’s bright red cock. He mostly holds the outer skin of the bottom growth only occasionally slipping a finger across the highly sensitive head. Every time he does, Caleb’s deep breaths and quiet moans turn to cries of bliss.

“What a responsive boy, hm?” Essek praises him as he writhes. “You like that huh? You like whatever I give you.”

A barely intelligible string of “yes”s spill from Caleb, and Essek, using this as a distraction, slips his first finger of his left hand into Caleb’s warm hole.

Pulsing tightly as Caleb cries in shock and pleasure the human’s wet cunt practically sucks Essek’s thin digit deeper in. Curling his manicured finger into Caleb’s walls Essek begins stroking his cock faster and thumbing the head more often.

Caleb has melted into a moaning shaking mess at the point that Essek pushes another finger into that tight hole. Searching for the area that never fails to make Caleb’s hips stutter, his fingers rub the soft soaked walls. With one push, Caleb bucks up involuntarily, letting Essek know he found the sweet spot.

Slowly plunging his fingers in and out of Caleb’s cunt at the same time as he quickly rubs that tantalizing cock, the human is so blissed out that he couldn’t help bucking into the feelings if he wanted to.

“Are you close, beautiful boy?”

“Yesyesyes, AH! Please, please, let me cum, scheiße, please!”

Planting a kiss on Caleb’s hipbone, Essek speeds up.

His fingers fuck into Caleb’s cunt so hard that sinful wet noises project throughout the room. Essek begins rubbing his thumb right on the head of Caleb’s cock. With both these sources of pleasure, Caleb lets out many fast and loud moans. 

Essek whispers sweet little nothings as he gazes at this partner, wracked with pleasure before he hears a final cry.

Caleb cries out and his body seizes at the crest of orgasm. His cunt locking down on Essek’s fingers and cock pulsing under his thumb, he lets out a continuous moan as he falls into waves of pleasure.

To guide him through, Essek resumes his motions slowly. This lets Caleb chase each aftershock until his cunt relaxes and his muscles ease.

Eventually, Caleb’s moan ceases and he’s left panting, while Essek no longer feels the orgasmic contractions on his fingers. Essek withdraws from his partner’s beautiful cunt and meets Caleb’s lips once more as he lies in the afterglow.

Peppering him with gentle kisses and praises, Essek can’t help but feel such pride for his love, "Such a darling boy, lets get you cleaned up hm?"

Caleb blinked up at him before smiling, "Yes, please."

**Author's Note:**

> And then Essek and Caleb took a nice relaxing bath before going to sleep!
> 
> Thank you for reading! Please don't be shy, I'd love any comments or kudos.
> 
> I have a basic list of kinks and pairings for the next month, but if you guys have any requests or suggestions, please leave them below!
> 
> Next up, Fingering with Beauyasha and then Bondage with Shadowgast!


End file.
